How to Talk to Your Employees About Their Careers


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What do your employees actually want out of their careers? What do they enjoy, excel at, aspire to, dream of? What skills are they lacking to actually achieve their long-term career goals, or do they even have career goals?

This article is designed to present a framework for considering career conversations, and offer a few ideas on techniques that can help you be supportive while talking honestly about an employee’s future career. As always, I’d love your feedback and suggestions, either over email or in the comments.

Why Bother Talking to Your Employees About Their Careers?

Having regular conversations about your team members’ career goals can have long-term, positive consequences for your relationships with your employees, employee retention, and job satisfaction.

Let’s start with the most basic, but perhaps least comfortable idea for many managers: your employees will probably leave you. Sooner or later, most of your employees will eventually find a different job. Some of them will move to a different role within the same organization, but many will leave your organization completely. A few will stick with you for years, and—rarely—others will stay for a lifetime.

And that’s OK. In fact, it’s totally expected. There are reasons to check in about career goals regardless of whether someone is going to be with you for one year or twenty.

For employees who will be transitioning in 0-5 years, career conversations can help you get the most out of the time you’ll have together. You can help them gain insight into their potential career opportunities, reflect back to them where you see their greatest potential, and offer them chances to improve the skills they’ll need as they head toward their ideal career. You’ll also benefit: employees that are gaining valuable experience and skills will have ample reason to stick around longer and, when they do decide to leave, it can be something discussed more openly and supportively, so you aren’t blindsided.

For longer term employees, career conversations can help ensure that they are regularly given new ways to sharpen and improve their skills, as well as transition in roles and responsibility in ways that make sense for both the employee and the organization. Together, you can craft a win-win situation, where they are gaining fulfillment from their careers over many years and the organization continues to benefit from their continued enthusiastic engagement.

Career conversations aren’t just for your strongest employees. Honest career conversations can help employees who are under-performing understand what opportunities are and aren’t available within your organization, and can help them learn what skills and insight they need to develop for the future, whether they stay at your organization or go elsewhere.

How to Frame a Career Conversation

I think good career conversations have three characteristics:

  1. Entered into without expectations. We are no longer living in an era where people climb a single career ladder within an organization. Many employees make lateral leaps in their career, or “step down” in order to maximize flexibility or satisfaction in their jobs. When setting up a conversation with an employee, let go of preconceived ideas about what “growth” must look like. It may not mean a new title, a bigger office, or more direct reports. Does your employee want to increase her interactions with the public? Does your employee want to pick up a new skill set that the organization needs and wants? Were certain projects especially fulfilling to her? Or maybe she’s serving as a caretaker for a relative and career “growth” right now means transitioning to work that allows her a flexible work schedule. Try to step into a career conversation without baggage about what career advancement looks like, and try to notice if you tend to think that “success” for someone else needs to mimic how you perceive success.
  2. Iterative. Some employees know exactly what they want their future to be and exactly how they want to get there. But for the rest of us, the future is a roiling mass of possibilities, uncertainties, and fears. The ideal future today may look wildly different from what it looked like two years ago. Career conversations can be iterative in a few ways. First, because your employee and you slowly gain more insight into what career path is truly the best match for her skills and passions. Second, because career paths can change. This can happen because of a serious life event—such as a health scare or change in family situation—or just because time and experience has impacted an employee’s goals and job satisfaction. It’s totally normal for someone to feel different about their career at 30 than they do at 55. Rather than lock an employee into a single path for “success,” offer flexibility for the career plan to change over months and years. Don’t be surprised if it evolves in ways neither of you were expecting.
  3. Collaborative.  You and your employee aren’t trying to simply come up with the best career path for her as an individual. Rather, you’re trying to find that perfect mix of what she wants to do, what the organization needs, and what she is good at. She may have more insight into the first, but as a manager you’ll have a lot of insight into the second and third. Reflect honestly where you see her skills and what brings the most value to the organization. As you continue to develop your relationship, search for ways that you can construct win-win scenarios, where your employee taps into her passion and skillset in a way that benefits the organization. Be willing to be active and engaged in helping show the employee ways she can contribute to the organization’s success.

Practical Career Conversations

Ready to actually try a career conversation? The first step is letting your employee know you’re up for it. Many people make the annual review process a place to check in on career development. I think there’s no harm in that as long as both you and your employee know that’s the plan. You might also decide you want to carve out time during your one-to-one meetings, or set up a dedicated meeting just to talk about career growth. Regardless of how or where you structure it, I’d suggest you tell your employee it’s coming.

When you’re scheduling the conversation, you might say something like, “I’d love to set up a time to talk about your career more generally. I know we can get stuck in focusing on day-to-day tasks, but I’d like to step back and talk about the future of your career. How about two weeks from now?”

That may feel very stilted to you, or not the kind of language you normally use with your team. Adapt the language to find something that does work. The key factors are that you signal that this will be a conversation at which you talk about their careers specifically and that you schedule it a little bit out. That ensures your employees have time to think about it, and hopefully they’ll be able to step back from their day-to-day work and think more generally about their career as a whole.

Once it’s been scheduled, I’d suggest that you as the manager take the lead in the conversation. I suggest you let them know why you’re having the conversation and what outcomes you are hoping to achieve.

Examples for why you’re having the conversation:

  • “I want to talk about your long term career goals so we can make sure you’re developing the skills you need over the next few years to achieve those goals.”
  • “I realize we’re always heads-down focused on the task at hand. I want to talk about your career more generally so that we can make sure you’re heading down a path that you find fulfilling that also helps the organization.”
  • “I really value you as an employee, and I want to make sure you’re fulfilled. I want to hear if you have thoughts about your career over the next few years, and talk about where I see you shine, so that we can keep an eye toward the future.”

What outcomes you expect:

  • “I don’t expect to figure everything out today. But I want you to know that I’m open to these conversations. I value your work, and I want you to start thinking about where you’d like your career to head.”
  • “This isn’t going to be a conversation where you come up with a finalized plan and present it and then I say yes or no. I want to collaborate on this, and give you a chance to think things through openly. Maybe you have a firm idea of where you’d like to be in 10 years, maybe not. Either way, I want to be able to start talking about it.”
  • “I know that people define success in many different ways, and I don’t want to presume what career growth looks like for you. I want to hear what matters most to you in your career.”
  • “By the end of this conversation, I’d like a better understanding of what work you find most fulfilling. And I’d like you to know where I am seeing a lot of potential for your growth.”

During the conversation, you can ask guiding questions to try to solicit information from the employee on what she finds most fulfilling and engaging, as well as offer your reflections on where you see the greatest potential for growth. Some guiding questions could be:

  • What projects did you most enjoy in the last year or two? Why?
  • You took on a new set of responsibilities with X project. Is that something you’d like to do more of in the coming years?
  • Are you enjoying collaborative work or have you been enjoying the solo projects?
  • What aspects of your work are you finding especially uninspiring? Why?
  • Have you seen other folks with career paths you find especially inspiring? What factors do you notice in those?
  • What are you looking for in your career?
  • What would you hope to change about your career in the coming years?
  • What skills do you want to develop in the coming years?

I also think it’s important that you reflect back to the employee the skills and experiences that are most beneficial to the organization. You might say things like:

  • I’ve been extremely impressed by X, and I was wondering if you had interest in doing more of that.
  • Your experience in X is a fantastic asset to the organization.
  • I appreciate X in your work.
  • You are very skilled at X.

When Passion and Skills Don’t Align

If you have enough of these conversations, you’ll notice that what an employee most wants to do doesn’t always align with what the organization needs or even with what she’s good at.

At a recent retreat, I heard other nonprofit leaders discussing the problem of “the firefighter who wants to be a ballerina.” I think of this as a metaphor for the nonprofit employee who is skilled at what she does now and fulfills a vital need for the organization, but her career goals are pointed at something else. Maybe she’s great at handling a crisis and keeping the organization afloat during even the most difficult of times, but during a career conversation she confesses that she wants to step away from the fray and focus on long-term projects. Or perhaps she’s part of your support team, but longs to move into programmatic work. Unfortunately, this firefighter has no experience being a ballerina. Even if you could shift her to a different role, the learning curve would be painfully high, and you’d have to replace her with someone who is less talented at firefighting.

Some people avoid having career conversations because they’re afraid this exact situation will arise, and their best people will ask to shift to roles where they aren’t qualified and aren’t helpful to the organization.

If you find yourself in this situation, know that you aren’t alone. Many managers have been where you are. Here are a few concepts you might consider if you find yourself in this spot. First, consider whether you can appreciate that at least this conversation is happening openly and with trust, instead of having your best firefighters secretly applying to ballerina roles at other organizations after hours. Second, if someone is expressing frustration with their current firefighter role, are there changes that can be made to make them feel more fulfilled in it? Third, are there small aspects of the ballerina role that could be integrated into her current firefighter work, so that she can continue firefighting most of the time but spend a percentage of her work on the ballerina tasks? (Though be careful about this one: you don’t want to end up with someone who works 20% more to try to add in extra ballerina hours while still holding down a full-time firefighter job!)

Fourth, remember that career goals change. Someone coming to you with dreams of being a ballerina today might find they’re less interested in that work in six months or two years, especially if they had a chance to dip a toe into it and found the waters less glamorous than they expected. So even if your very best people are in the firefighter/ballerina dilemma, remember to take a few deep breaths, be a little flexible, and give it some time. Maybe they’ll eventually leave you to pursue that ballerina life full time, but there’s a good chance that if they feel supported, heard, and appreciated and can integrate a touch of ballerina in their current roles, they may remember what drew them to firefighting in the first place.

Finally, remember that the worst case isn’t that bad. If your very best firefighters are hell-bent on becoming ballerinas, and they are terrible ballerinas, and your organization doesn’t need ballerinas, it’s actually OK. You can still acknowledge their interests and your limitations clearly and empathetically. That acknowledgement might sound something like: “I hear you’d like to work on more long term projects, which you have less experience with. Right now, you are doing fantastic work on the quick-response projects, and I want to keep you there for as long as you’re willing. I’m not sure that there’s ever going to be a full time role for you in the long-term project department. But I’m glad we’ve started discussing it. I’ll keep my eyes open over the next year for opportunities to help you build those skills while keeping you in your current department. I’d like you to think about it more, and let’s keep this discussion going. I’d like you to find fulfillment in your career, even if that might mean you go to another organization one day.”

Your firefighters may not want to hear that, but at least they’ll know where they stand. Even better, you’ll have created a relationship built on honesty.

Uncertainty is Fine

If you start chatting with your employees about their careers, don’t be surprised if a few of them are a bit mystified at the idea of a career trajectory. You may find the conversation stilted, uncertain, or even a bit suspicious. Such a conversation can also be successful. You’ll still have an opportunity to flag your investment in your employee as well as talk to her about what skills she’s bringing to the organization. Knowing that your employee is uncertain about her career goals is also useful for you; it can prevent you from making unnecessary assumptions about where she’d like her career to head.

Try to take the pressure off and acknowledge that uncertainty is fine. You might try starting smaller: what are a few tasks or projects she enjoys? What skills does she want to develop? It doesn’t necessarily have to lead anywhere right away.

Don’t Drop the Conversation

If you’ve had an initial conversation with an employee and established a good dialogue, then try to keep it going. Schedule a time later in the year to discuss it more. Look for key take aways from your early career conversations. Were there skills your employees hoped to develop? Projects that would give them valuable experiences? Remember to keep that career discussion in the back of your mind and remember it when you prioritize projects, responsibilities and opportunities. When you schedule your next check in, talk about those choices.

Want to discuss this more? I’d love to hear about your career conversations. Please shoot me an email and let’s start a discussion.


6 Lessons I Learned in the First 6 Months of Nonprofit Management Consulting


CC BY-ND 2.0 Deveion Acker

Last October, I offered up a bundle of my ideas, dreams, and experiences, granted it a name and a business bank account, and launched it onto the World Wide Web: Groundwork Consulting.  Groundwork was a way I could formalizing and publicize work I’d been doing for years on the side: working with friends and acquaintances in the nonprofit world to tackle management challenges and think through new opportunities.

Six months later, I realize I’ve been learning a ton about nonprofit management consulting without a lot of chance to reflect on it all. So, here’s a listicle of lessons to commemorate the journey so far:

  1. You can’t change other people. You can only support them in changing themselves. I think this is a lesson I will be blessed to learn again and again in my consulting work. As a management consultant, I can’t make someone change. When talking to a client who has slipped back into a bad pattern, I sometimes wish more than anything that I could just do the work for them. But that’s doesn’t actually help anyone. Only the client can ultimately do the work. My job is just to be a coach, a collaborator, a sounding board, a guide, and a cheerleader in their process. The process can be slow and stumbling at times, but it’s their journey and I need to be present to support it. 
  2. My job is to see the best version of my clients. The more I do this work, the more convinced I become that my ultimate work is to believe in the best version of someone else, and reflect that vision back. No matter how down a client may feel on where they are in adopting changes, my job is to keep strong in the belief that they can and will reach their ultimate potential. The world is full of doubters and nay-sayers. But through my consulting work, I get to always believe in the best in others. 
  3. Nonprofits are systems whose problems must be viewed holistically. Sometimes a client wants me to help address one small piece of the organization. But no sooner do we begin than all the connected problems and concerns start rearing up, demanding attention. Fixing any one problem requires stepping back and looking at the whole picture. 
  4. Changes have to be made one tiny bite at a time. Success helps clients feel optimistic and engaged, and helps them believe in the process. But if they bite off too much, they’re destined to trip up. So my job is to make it easy by drilling down to a single, achievable thing that we can change right now, and then moving on to the next step only once the first change has been mastered. 
  5. Relationship problems are the root of many organizational problems. Sometimes nonprofits come to me wanting solutions to what they see as huge organizational problems around structure and strategy. And while it can be useful to get aligned on structure and strategy (and I love hosting those conversations), many of the day-to-day issues boil down to relationship issues. These look like communication problems, unresolved jealousies, hurt feelings, and broken trust. Fixing the relationships makes all the other problems easier to address. 
  6. I need to practice what I preach. Even as I have advocated for other people to believe in themselves, practice self-empathy, repair relationships, and adopt big changes by splitting them up into manageable bites, I see countless ways I fall short in these respects. As I look at the next six months, I’m recommitting to holding myself to the same ideals I hold my clients, including making sure that I’m not letting the work run my life. 

I’ve had a lot of other moments of insight along the way, but not all of those lessons fit neatly into a list like this. So I’ll leave it there for now. And if  you’re interested in my nonprofit consulting services or just want to brainstorm about management challenges you’ve been facing lately, drop me a note and let’s chat.

Waitlist for Summer 2017 Now Available

I’m pleased to announce that I’m opening up a waitlist for future clients.

For background: I strictly limit how many clients I see at any one time. This ensures I can continue to be fully present for the organizations that I have already committed to—the Electronic Frontier Foundation and Freedom of the Press Foundation—and to my existing clients. In order to balance all of these things and still have time for a family, I’ve chosen to take on no more than 3 clients at a time.

I’m thrilled to say that I’m at capacity right now, and will be for several more months. I expect to have availability to take on additional clients in June or July of 2017.

f you’re interested in coaching, please fill out my contact form and let me know what you’re looking for, and I’ll add you to the summer waitlist. I’d urge you to get in touch with me sooner rather than later, as the waiting list may fill up.

As always, I offer a sliding scale to ensure that those who need it most can afford coaching. It is also my intention to continue to have pro bono clients regularly, so that I can be of service. So if price is a barrier, please know that I’ll try to work with you.

The principle behind Groundwork is simple: nonprofit leaders and managers should have the support and guidance they need to excel at their jobs. Too often, nonprofit leaders are juggling five jobs, working with few resources, and are choosing their job over their own health. They may not have the support system they need to make difficult and even unpopular decisions, resolve conflicts in the workplace with compassion, and create the kind of worklife that is fulfilling, sustainable, and truly impactful. Groundwork provides individualized, custom coaching so that you can de-stress, improve productivity for yourself and your team, take your organization to the next level, tackle the challenges ahead, and love your job.

If you’re looking for a management or leadership coach but don’t want to wait till the summer, please let me know. Over the last few months, I’ve developed a network of nonprofit coaches with similar guiding principles. It would be my pleasure to find out what you need and then connect you to one of them.

Ready to take the next step? Contact me to get on my summer waitlist.

Better Than a New Year’s Resolution: A Thank You Letter

writers-desk-with-cappuccinoIt’s a new year, which brings a new opportunity to create the life you’ve been longing for.

It’s a chance to give deep reflection to where you’re trying to head in your life, and maybe start committing to taking a few steps to get there.

On this blog, we tend to discuss career goals and organizational health. But this time of year is also great for thinking through goals and hopes for your whole life—work, personal, physical, mental, etc.

Lots of people like to make New Year’s resolutions. Maybe you call yours an intention instead of a resolution.

But New Year’s resolutions can be a bit unyielding. If your life and circumstances change, making the possibility of achieving a resolution unlikely, it can be demoralizing. It might feel like failure. And if life opportunities and circumstances change, you want to make sure you aren’t locked into a resolution that doesn’t make sense for your path anymore.

This year, I’m avoiding a full-blown New Year’s resolution in lieu of an exercise I hope will be more forgiving, insightful, and meaningful: a New Year’s thank you letter.

Want to try it? It’s simple.

First, take a few minutes to imagine where you’d like to be headed in your life. Imagine it’s a year or two down the road, and things are really going well for you. How do you spend your days? How do you feel? What have you invested more of your energy in? What have you given up or turned away from? How are your relationships? How is your health, your savings, your career? Sit and picture this for a few minutes, and imagine you are really there, in that better place.

Often, we have a sense of what we want our future life to be, even if that’s just because we know what parts of our lives are causing friction right now. Feel free to really step into the role for a while.

You may find yourself holding back, thinking: That’s unrealistic. I won’t get there in a year, or even more. Try to set those internal fears aside and just imagine, at least for a bit, that your life really can be where you want it to go.

Now, start writing the letter. It’s a letter that future you is writing to current you. And you are thanking yourself for taking the steps you need to take to get to that better place.

Future You might have a lot to say—reassurances that the difficult times will get better, acknowledgement of the hard work and sacrifice that will be necessary. The journey ahead might take some courage, some persistence. But remember to write the letter from a state of deep fulfillment, knowing that you have gone through the hard times and on to the better part of your life. Write as if everything worked out for the best.

It can be useful to describe the life Future You is enjoying. Talk about relationships, career, joys, current challenges, and how things have changed with time.

But remember that this is ultimately a thank you letter. Thank yourself for the work you did. Try to tap into that gratitude.

Then give whatever salutation seems most appropriate and sign it “Your future self.”

That’s it. Be open to whatever you notice in the process. And then close it up and keep the letter nearby and reread it whenever the time feels right. It can serve as a reminder for where you are going and why you want to get there.

5 Facilitation Hacks for Large Groups

Last week I finally made it out to part of the Nonprofit Dev Summit hosted by Aspiration. I had hoped to be there all three days, but work obligations got in the way. While there, I noticed a few tricks that I thought helped create a space that was more safe and inclusive, techniques I plan to unabashedly steal the next time I’m working with a very large group of folks who don’t know each other:

  1. Lanyards colored-coded for photo privacy. As a privacy advocate by profession as well as by passion, this one delighted me. Participants were offered two lanyard choices when they arrived: blue and red. Blue indicated that the participant didn’t mind being caught in photos, whereas red meant no photos as all—including being in the background of someone else’s photos. This can bring a small but important measure of comfort both to folks who may risk their lives to attend activism events as well as for anybody who wants to minimize their digital footprint.
  2. Pronoun options on nametags. Participants were invited to indicate their gender pronoun in Sharpie on their nametags when they first walked in. (Learn more.) I loved this because it surfaces pronoun preferences visibly whenever you are speaking to someone. I also appreciated that it was entirely optional—no one had to put themselves into a pronoun box if they didn’t want to, or publicly indicate anything about their pronoun at all if it would make them uncomfortable.
  3. Clearly identifying who can be approached if a problem occurs. I really appreciated how every person affiliated with Aspiration was named and publicly acknowledged at the beginning, with the specific suggestion that these folks could help out if at any time someone in the conference felt uncomfortable or concerned. Two improvements I would make to this: give staff members a special shirt or hat, so that folks can identify them at a glance in a crowd; repeat the process of identifying staff members multiple times. I wasn’t there the entire conference and so I can’t say whether this was repeated, but it’s the type of information I think needs to be reiterated a few times throughout the event for latecomers. I also hope these staff members were available during after-hours events, since I imagine that may be where many issues could crop up. (I didn’t go to any of the happy hours connected to the conference.)
  4. A preference for plain language. The conference organizers specifically asked that participants use plain language, avoiding inside-baseball jargon and acronyms. (For example, “teaching the trainers” instead of “TTT” or “The Electronic Communications Privacy Act, the law governing email privacy” instead of ECPA.) This is so necessary for international participants for whom English is a second language (there were many) as well as anybody who might be easing into a topic for the first time. No movement can grow unless it can welcome in newcomers, and language choices can either alienate or invite participation from new folks.
  5. Diversity in participant-leaders. Aspiration’s meeting facilitation style relies heavily on creating small groups run by facilitators who are themselves attendees of the conference. This generally requires Aspiration to ask a number of people at the conference to serve as small group facilitators. (While people can volunteer, often Aspiration ends up requesting people take on this role.) I noticed that the facilitators chosen were diverse—people of color, people across the gender spectrum, and people from a range of different age groups. I did a quick tally while I was at the event, and it seemed that about half of the group facilitators were female-presenting. I don’t know if that was done intentionally, but I appreciated it.

This isn’t a comprehensive list of everything the conference did to create comfort for the participants, nor is it a list of everything a conference should do to be inclusive and safe (if you know a good list for the latter, please let me know because I’d love to read it). But as I’ve been thinking more about large group facilitation, I appreciated seeing these practices work seamlessly at the conference.

On Nonprofit Leaders Navigating the Trump Election


by Michael Vadon (CC BY-SA 2.0)

Organizations across the country were shaken by the election of Donald Trump. If you work in a libertarian or progressive organization, a civil liberties or environmental group, a nonprofit defending reproductive choice or the rights of the LGBTQ community, or any organization working toward immigration reform, prison reform, or racial justice, this election is bad news. And frankly, it’s bad news for many other advocacy groups as well.

If you’re a manager or leader at one of these nonprofits, then this is a critical time for you. Your team and others will be looking to you for support and reassurance, your organization may be processing a wide range of emotional reactions, and your long term plans may need to be reshuffled.

Here are four things to keep in mind as the next few weeks unfold:

  • Give your people space and time to process in their own way. Some folks in your organization may be shell-shocked and overwhelmed. Others may be furious. Some will be seeking answers and ready for action. Others will be afraid for themselves, their friends, and their family. Don’t expect everyone to process this moment the same way you do. Instead, create space. Leave your door wide open for deep, non-judgmental, empathetic conversations. This may take a day or a few weeks, but in the long run your team may be closer and more connected than ever before.
  • Be honest. It can be tempting to try to tell your team that “everything will be OK.” You might think that this will help your team feel better. Instead, they may think you don’t understand or recognize the severity of what’s occurred. Long term, your team will respect you more and be better prepared for the future if you are honest with them about the challenges this election creates for your work. This a great opportunity to practice being supportive and welcoming without trying to fix or downplay someone else’s fears.
  • Revisit your 6 month, 1 year, and 5 year plans. The election results may put you in a different place on a range of your issues. While it’s too early to know specifics, you may need need to work with your key staff members to revisit and revise your future plans.
  • Be gentle with yourself. This election may have caused some fear and uncertainty in your own life. You may be struggling to come to terms with it. Don’t just make yourself a support system for other people. Give yourself space to acknowledge your own feelings, find friends you can talk to, and take steps to make sure you’re taking care of your own heart and mind right now. Remember: you’re needed in the fight ahead.

The next few weeks and months might be difficult times for some members of your organization, but they also bring a lot of opportunity. This is a time to engage with more supporters, showcase the value of your work, and build a stronger movement. Many will be galvanized by this election to increase their involvement in mission-driven nonprofits, so this could well turn into a time of growth and energy. Internally, such times can be a mixed bag—stress fractures that have been hidden just beneath the surface may spring up or teams may find they bond deeply. It’s also a chance for everyone in your organization to anchor themselves in the mission. In any case, the next few weeks can be a defining time for your organization and for you as a leader.

So walk into this time with an eye open to the lessons and opportunities just below the surface, and practice some gentleness toward yourself and others in the process.

Moving Beyond Your Success

stopA few years ago, I had a conversation with an acquaintance who introduced me to an idea that blew my mind:  the very things which made someone successful early in her career could prevent growth later in a career.

Wait, what? How was that even possible?

My acquaintance suggested I read What Got You Here Won’t Get You There by Marshall Goldsmith with Peter Reiter, which I recommend to any successful person who feels like she’s inexplicably plateaued. The concepts in the book influenced my thinking on this issue, so I mention it now to give due credit. However, my ideas diverge from the author’s in a number of key ways. For example, one of the main ideas of the book is that successful people are successful in spite of certain qualities which later limit their growth. I actually tend to go a step further: sometimes, successful people may be successful because of certain qualities that later limit their growth.  So think of what follows as my personal interpretation of certain ideas first introduced by Goldsmith, not a summary of the book.

One idea that stemmed in part from the book is that successful people often suffer from delusions about why they are successful.

The Why of Success

Imagine a man putting on a pair of brown shoes on Tuesday, walking down the street to the gas station, and buying 3 five dollar lotto cards. Imagine he wins a few thousand dollars. He comes in again every few days, playing a range of different types of scratch cards, not winning. (Yes, it happens: my first job out of college was at a gas station and I had a lot of repeat customers for lotto cards.) And then one day he wins more money, again while wearing those same brown shoes, playing five dollar scratchers, on a Tuesday. All of a sudden, he’s got a pattern that seems successful: shoes, five dollar scratchers, Tuesdays, this gas station.

Of course, he’s wrong. But humans love patterns; our brains seek them out.

Highly successful people may have used a wide range of techniques to generate early successes in their careers. But successful people can fall into the same trap as the lotto playing guy: it feels like there’s a connection, there are facts and data and positive outcomes, but they’re still totally wrong about the why of success. Success could have been coincidental, or it could have hinged on factors you aren’t considering.

Other times, successful people use techniques that directly and transparently impact the successful outcome. The example that comes to mind is a woman who asks for more during a salary negotiation and is rewarded with a higher salary from a boss who would never have otherwise considered it. We don’t know exactly the root of the success—was it how she asked? Or was it simply that she asked at all? Were there other ways to negotiate for more money that would have been even more successful? But we know that there was some relationship between this action and that outcome. She created a success, and future successes may lock her into a set of beliefs about how successes are created.

Sometimes we overestimate our own contributions. We may believe a success came as a result of a specific technique or skill, when in fact the same outcome could have been brought about through other means. We become rooted in a particular pattern of behavior or thinking, unable to differentiate between those factors that have an influence on real success—like deciding to speak up in a salary negotiation—from those that are coincidental—like wearing brown shoes and buying lotto cards only on Tuesdays.

Worse, we may even try to apply these coincidental techniques to situations that are completely unrelated. Think: the lotto guy wearing brown shoes to a salary negotiation.

We may begin to believe that patterns we associate with certain successes—which are actually unproven theories—will work to create successes in wholly different circumstances. I think of this as superstition of success.

How Superstition of Success Holds Us Back

Patterns can become deeply rooted in our psyche. You may even begin to believe that characteristics you associate with your successes are unchangeable characteristics of your personality.

And that’s risky. It creates blind spots in our own lives and could prevent us from developing skills and traits that would provide necessary balance to skills we developed early in life. These imbalances can end up holding people back in ways that can be hard to recognize. Let me sketch out a few potential examples —based on real people I’ve encountered over the years:

A man early in his career demonstrated tenacity, boldness, and a tendency to speak out directly. People gravitated toward him and considered him a natural leader. But as time went on, people he worked with began to see him as unyielding, too quick to act without considering all the facts. Coworkers thought he was a poor listener. When a senior role opened up in his organization, he was never considered; everyone assumed he was too bull-headed and unyielding to be elevated into a role requiring subtlety and care. Perhaps worse, he had no idea. He believed that his tenacity and boldness were exactly what had made him so successful up until then. And in fact, he believed they were indelible facets of his personality: that he was a bold, visionary man who would tell it like it was and stick to the end goal.

Whether or not he was right that these characteristics had contributed to early successes, these habits had stalled his career in ways he couldn’t imagine. Unable to move ahead in his current organization, he simply went to another organization, where his no-bullshit communication style and commitment to achieving results dazzled new coworkers all over again, which reaffirmed his belief that these qualities were necessary to achieving success. This set him up to stall out in exactly the same way, a pattern he could repeat as often as he’d like over the course of his career.

Now take a senior executive who is liked by almost everyone and considered a conscientious listener. She works long hours, often taking on overflow work so that her employees can go home at the end of the day.  Everyone adores her. She considers herself a deeply compassionate and caring person, and she considers those characteristics unchangeable features of her personality. But she keeps losing her best people because they aren’t challenged or given chances to grow. In her efforts to protect employees from the most difficult work, she’s robbed them of opportunities to take on difficult challenges and stretch their wings. Ambitious employees hungry to prove themselves gravitate to other organizations where they can be at the center of things, and the employees that remain exploit the woman’s generosity and kindness, knowing that she won’t ever fire them. The executive finds that the only way she can grow her organization is to simply heap more work upon her own overburdened shoulders, until she is so exhausted her health begins failing.

These aren’t just hypothetical scenarios: I’ve met more than one person who fits each of these models. In fact, I can think of three people who fit the first scenario pretty specifically, and two people who are a pretty exact match for the second—dismal outcomes and all!

12 Bad Habits of Somewhat Successful People

Goldsmith outlines 20 “transactional flaws” in his book, basically bad habits of interpersonal behavior that successful people often adopt.  These are the type of habits that successful people may employ early in careers—intentionally or often unintentionally—which ultimately limit their growth.

There are about 9 of these “transactional flaws” that I see frequently among highly successful nonprofit professionals (descriptions excerpted from Goldsmith’s book):

  • Winning too much: The need to win at all costs and in all situations—when it matters, when it doesn’t, and when it’s totally beside the point.
  • Adding too much value: The overwhelming desire to add our two cents to every discussion.
  • Passing judgement: The need to rate others and impose our standards on them.
  • Speaking when angry: Using emotional volatility as a management tool.
  • Withholding information: The refusal to share information in order to maintain an advantage over others.
  • Claiming credit that we don’t deserve: The most annoying way to overestimate our contribution to any success.
  • Clinging to the past: The need to deflect blame away from ourselves and onto events and people from our past; a subset of blaming everyone else.
  • Playing favorites: Failing to see that we are treating someone unfairly.
  • The excessive need to be “me”: Exalting our faults as virtues simply because they’re who we are.

To this list, I’d add a few I think are special favorites among nonprofit professionals:

  • Acting like a martyr: Inflicting self-suffering to complete work in an unconscious attempt to garner sympathy, social credit, and admiration.
  • Indecisiveness in the name of consensus: Allowing even small decisions to grow into time-sucking debates, often accompanied by a belief that absolute consensus must be achieved on all issues or that every decision benefits from a popularity contest.
  • Unproductive kindness: Rooted in a deep desire to be liked by others, this can result in nonprofit managers refusing to have hard conversations, make unpopular decisions, terminate employees that are not working out, and do any number of other things to be liked by all parties. They may even pass these hard decisions on to other managers.

Sometimes it’ll be easy to look at a list like this and immediately see which characteristics apply to your own professional life. Nobody is perfect, after all; it’s impossible to be the perfect, compassionate, honest communicator every moment of every day.

But I think that often we really don’t know how we come across. We may have a personal narrative about our lives that is wildly different from how we are perceived by coworkers. You may consider yourself a hard-working, well-liked, efficient, and direct manager, while others see you as brusque, a brutal task master, playing favorites, and impatient.

The first step is getting to the root of how you are perceived by others and then use that to tease out what bad habits, transactional flaws, or unintended messages you may be conveying.

A good starting point is listening.

Don’t Flinch: A Self Assessment Tool

One way to start unravelling our own self-limiting habits is to pay meticulous attention whenever someone describes you. Hone in on the exact words, and try to note them without judgement or defensiveness. I’d even advise collecting them in a notebook or document of some form, so you can look for trends over a week or two.

You should also ask people to give you feedback—what do I do well? What do I need to work on? It’s worth asking this of people you know well as well as those you know pretty casually; sometimes a casual coworker will have insights our closest coworkers are blind to. It’s OK—in fact, it’s very illuminating— if this list is substantially different from how you see yourself.

Once you have a good list, try to stretch yourself to imagine what might be missing.

Are you making trade-offs along the way to success? Do people see you as a caricature of how you see yourself, honing in on the most obvious traits and not seeing the other components of you? Have your successes come with interpersonal costs, or with personal ones?

Occasionally, people will be very blunt in their feedback. “You’re impatient and you never listen to other people,” a coworker might tell you.

Other times, the feedback will be couched in much gentler terms. You may have to spend some time searching for what the underlying message is. You may hear that you have high standards, get the job done no matter what, or are always nice. And deep down, these same coworkers may think that you judge everyone by your standards, are an obsessive workaholic, or have no backbone.

It can be useful to actually make a chart of the qualities you associate with your success or that people associate with your successes, and then stretch yourself to imagine what might be missing.  For example, your list of personal success qualities might looks something like this:

  • Always delivers projects
  • Meticulous
  • Likeable and kind
  • Busy

Nice characteristics, right? It’s easy to see how we might think these characteristics are important and even necessary to success. But let’s tease out some of the hidden possibilities for how a seemingly positive characteristic could be interpreted by others, have unintended negative consequences, or can lock us into habits that limit growth. I’ll call these negative characteristics “shadow qualities” since they often lurk in the shadow of the very qualities we associate with success.

Qualities associated with your prior successes Potential shadow qualities limiting your growth
Always delivers projects
  • Willing to sacrifice anything to get a project done, including burning yourself out
  • Willing to run over others to deliver the project on time
  • Judgemental of others who are less productive
  • Not ambitious; unwilling to reach for stretch goals whose results are uncertain
  • Convinced on your own perfection and the necessity of your own contribution; egotistical
  • Unyielding
  • Micro-managing
  • Unwilling to share in responsibilities
  • Judgmental of the shortcomings of others
  • Certain you know the one true way of doing things
  • Self-hating; unable to live up to your own standards
  • Creating anxiety among those around you
  • No fun
Likeable and kind
  • Unable to make hard decisions
  • Unable to have frank, difficult conversations
  • Always available as a support for someone else, even when it inconveniences you
  • Unwilling to make unpopular decisions—or sometimes even seriously consider them!
  • Unavailable
  • Can’t see the forest for the trees
  • Constantly chasing unachievable goals
  • Burning yourself out
  • Skeptical of the priorities of others
  • Distant from coworkers

To do this exercise well, it’s imperative to stretch your imagination a bit. The point is to try to tease out potential blind spots and trade-offs you’ve been making unconsciously. The right side of the chart might be very uncomfortable, full of things that you’d even reject at first blush.

Do it anyway. Sit with the idea that you’ve lost something in the pursuit of success, and this is the first step to starting to repair it.

It may help to walk away for a few days and come back to this list with fresh eyes, and ideally getting feedback from a few other people about whether any of the “awfuls” on the right side of the chart could apply to you.

Not everything on the right side will apply, of course. Thankfully! But probably a couple of those uncomfortable traits on your list will ring true for your own life.

Now What?

If you’ve been successful in your career, it can be easy to find yourself trapped in certain ideas about why you were successful. Too often, those ideas are based as much on superstition as on fact. In turn, these ideas about success can limit your growth.

The good news is it doesn’t have to be that way. It is possible to build a new set of habits and move beyond the characteristics that defined you early in your career.

Awareness is where we start. But then it’s time to delve into the real work. Healing troubled work relationships and reinventing yourself is hard, time-consuming work. I’m not going to attempt to cover that process here, but I would recommend Goldsmith’s book as a starting place, though I consider his prescription for change most appropriate in the most dire of circumstances. And if something in this article resonated with you and you’d like to start tackling these imbalanced in your career life, please contact me about coaching.

Finally, I consider this article to be a working document with my current thoughts on the matter, and I recognize that there are a range of views and experiences beyond my own. I’d love to hear your experiences, thoughts, and ideas. Please consider leaving me a comment below or send me an email if you have thoughts to share.

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